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To overcome the structural limitations of existing inherently chiral macrocyclic systems, which often suffer from facile racemization due to conformational flexibility, we report herein an asymmetric synthesis of a new class of inherently chiral double\u2010macrocyclic molecules through an intramolecular macrocyclization strategy, employing calix[4]arenes as the starting platform. Catalyzed by [Pd(allyl)Cl]\n                    <jats:sub>2<\/jats:sub>\n                    and a chiral phosphoramidite ligand, calix[4]arene derivatives bearing a monoaryl bromide linker at the upper rim underwent a facile enantioselective remote transannular Suzuki\u2013Miyaura coupling with the adjacent upper\u2010rim position of the neighboring arene unit, furnishing the desired inherently chiral double\u2010calixarene macrocycles in up to 71% yield and 91%\n                    <jats:italic>ee<\/jats:italic>\n                    . The resulting double macrocycles feature stable conformations and unique semi\u2010enveloped chiral cavities, and exhibit promising chiral catalytic and chiroptical properties.\n                  <\/jats:p>","DOI":"10.1002\/anie.7110885","type":"journal-article","created":{"date-parts":[[2026,9,27]],"date-time":"2026-09-27T16:33:06Z","timestamp":1790526786000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Catalytic Enantioselective Remote Transannular Desymmetrization of Calix[4]Arenes to Inherently Chiral Double\u2010Macrocycles"],"prefix":"10.1002","author":[{"given":"Yue","family":"Zhang","sequence":"first","affiliation":[{"name":"Key Laboratory of Bioorganic Phosphorous and Chemical Biology, Department of Chemistry Tsinghua University  Beijing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xin","family":"Zhang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Bioorganic Phosphorous and Chemical Biology, Department of Chemistry Tsinghua University  Beijing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2131-065X","authenticated-orcid":false,"given":"Lu","family":"Yu","sequence":"additional","affiliation":[{"name":"Key Laboratory of Bioorganic Phosphorous and Chemical Biology, Department of Chemistry Tsinghua University  Beijing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9946-0810","authenticated-orcid":false,"given":"Qing\u2010Hui","family":"Guo","sequence":"additional","affiliation":[{"name":"Key Laboratory of Bioorganic Phosphorous and Chemical Biology, Department of Chemistry Tsinghua University  Beijing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2545-807X","authenticated-orcid":false,"given":"Ruimao","family":"Hua","sequence":"additional","affiliation":[{"name":"Key Laboratory of Bioorganic Phosphorous and Chemical Biology, Department of Chemistry Tsinghua University  Beijing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7112-0657","authenticated-orcid":false,"given":"Mei\u2010Xiang","family":"Wang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Bioorganic Phosphorous and Chemical Biology, Department of Chemistry Tsinghua University  Beijing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7982-2546","authenticated-orcid":false,"given":"Shuo","family":"Tong","sequence":"additional","affiliation":[{"name":"Key Laboratory of Bioorganic Phosphorous and Chemical Biology, Department of Chemistry Tsinghua University  Beijing China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,27]]},"reference":[{"key":"e_1_2_8_2_1","volume-title":"Calixarenes","author":"Gutsche C. 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